Top drive motors (i.e., drilling motors for driving a drill string and a bit attached thereto to form a borehole) are typically air cooled via a blower. In harsh weather environments, the blower may intake rainwater, which in turn may enter a junction box which houses a variety of electrical components (e.g., buss bars and other electrical disconnects). One potential leak path on top drive motors is along the various wires, cables, conduits, and tubes which extend from the motor to the junction box on the top drive (e.g., water may tend to wick along wires, cables, tubes, and conduits penetrating into the junction box). The presence of water in the junction box may damage the various electrical components housed in the junction box and create an electrical shock hazard for workers. Accordingly, the present invention is directed to a sealing system for creating a water tight seal around wires, cables, tubes, and conduits, passing through an aperture. In one embodiment, the sealing system of the present invention is configured to create a water tight seal around wires passing from a top drive motor and into a junction box, although the present invention is not limited to such applications.